Because Six Chipmunks Never Make Things Simple
by SWAGlolita
Summary: Brittany's power hungry, Eleanor's in a crisis, Jeanette's rebelling, and the Chipmunks have a crazy bet to see who can get a girlfriend first. They're all in Australia. Of course these six chipmunks won't make things easy and fall in love the simple way.
1. The Bet

**Okay, so this is my first Chipmunks x Chipettes story that at first I mostly planned on just making it Simonette, but it did not turn out that way :). Anyway, the song the Chipettes finish singing at the end is "Put Your Records On" which was in the Squeakquel. The whole story takes place AFTER Chipwrecked. R&R, please 3**

* * *

**CHAPTER 1**

"So," Alvin said loudly, "why haven't you taken Jeanie out on another date yet, Simon?"

Simon glared at him. This was a touchy subject. "That was _Simone_. There is absolutely nothing going on between me and Jeanette."

"But you want there to be!" Alvin sang out in a teasing way. He bit into an apple that was practically bigger than him.

"So?" snapped Simon.

"So ask her out. As you," Alvin stated, biting into the apple again. "And you two can live happily-ever-after in your nerd romance."

"We're not nerds," Simon said for the thousandth time. "We simply value our education, unlike you or Brittany. And it's not that easy."

"What's not that easy?" asked Alvin. In only a few minutes, his gigantic apple was already half gone.

"Asking a girl out on a date," Simon answered in an exasperated tone.

"Oh come on," Alvin snorted. "Yes it is."

"Let's see you do it then," Simon shot back. "Go and ask Brittany on a date. Right now."

"Fine," Alvin replied, not moving at all from his spot on the kitchen table. Simon raised an eyebrow at him.

"That's not fair!" Alvin whined. "Brittany will hit me if I ask her out! Can I just do Eleanor instead?"

"What?" Theodore shrieked, having just walked into the kitchen looking for a snack. "Alvin's asking out _Eleanor_? Isn't Brittany a little more his type?" He looked up at Alvin hopefully.

"Looks like Theo's got a thing for Eleanor!" Alvin crowed, wiggling his eyebrows. "Don't worry, she's all yours. I'm just trying to get Simon to ask out Jeanette."

"Why should I listen to you, when you're too scared to ask out Brittany?" Simon asked pointedly.

Theodore popped some cheese balls into his mouth. "I didn't know Alvin was scared of Brittany."

"I'M NOT!" shouted Alvin. He took a furious bite of his apple.

"Prove it," Simon smirked. He was enjoying making Alvin squirm for once, instead of it being the other way around.

"Not until you ask out Jeanette," growled Alvin. He was pretty confident that _that _was never going to happen.

The two brothers glared at each other from opposite sides of the kitchen table, while Theodore sat in the middle, stuffing himself with cheese balls.

"Don't fight, you guys," he pleaded with them. "No one has to ask anyone out."

"Simon does," Alvin huffed. "Otherwise he'll be alone for the rest of his life."

"And you won't?" Simon jumped up, all his fur sticking straight up, on edge.

"I'm Alvin Seville," Alvin replied cockily. "Girls are practically throwing themselves at me."

"I don't see Brittany throwing herself at you," retorted Simon.

"Are you saying that you don't think I can get Brittany?" Alvin demanded.

"I _know_ you can't," Simon shot back.

"Well, I know that there's no way you'll ever work up the nerve to ask out Jeanette," Alvin snapped.

"I've already saved her life, I think I can do something as simple as ask her out," Simon replied with a sudden burst of confidence.

"Guys -" Theodore started, but Alvin cut him off.

"Wanna bet on that?"

Simon narrowed his eyes. "You're on."

"_Guys_!" Theodore raised his voice an octave.

"First person to get a Chipette as their girlfriend wins," Alvin said, laying down the rules. "No one's allowed to tell any of the Chipettes about the bet. And don't trash-talk each other to the Chipettes … any more than normal."

"And when I win?" asked Simon.

"_If _you win, dear brother," Alvin said with a malicious smile, "I'll do whatever you want for a week. I'll be your slave. But if I win, then you have to be _my_ slave."

"Guys," Theodore tried again.

"Deal," Simon said quickly, and the two Chipmunks shook on it.

"GUYS!" Theodore screamed, finally catching their attention.

"Oh, Theo, did you want to be part of the bet, too?" asked Simon.

"Sorry," added Alvin. "Of course you can be in it! As long as you go for Eleanor."

"I-" Theodore started, but the other two had already left the kitchen. He was there all alone, except for the now totally empty pack of cheese balls.

He actually hadn't wanted to be part of Alvin and Simon's weird bet. He'd just wanted to know if there were any more cheese balls. But it seemed like now he was stuck in the bet, and even worse, without any cheese balls.

* * *

_"You're gonna find yourself somewhere, somehow,"_

Eleanor sang the last line of "Put Your Records On", the Chipettes finished off their last dance move, posed, and then good-naturedly collapsed on the floor.

"Okay, girls, take five," Brittany announced from the ground.

"Take five?" shrieked Eleanor. "We've been practicing this song for two hours, Britt! How about rehearsal over?"

"Please, Brittany?" Jeanette chipped in.

"Well, alright," the pink Chipette consented. "But do you think we really have this one perfect?"

"Absolutely," Eleanor reassured her. "You worry too much, Britt."

"I just want this concert to be perfect," Brittany sighed. "And if practice makes perfect, we definitely need a lot of practice."

"But this isn't our first concert," Jeanette pointed out. "And we're not competing against anyone. So what's making it so important?"

"It's not the concert itself ..." Brittany trailed off, and then she sat up abruptly. "Does it ever bother you that we're not as famous as the Chipmunks?"

Eleanor thought about it for a moment. "No," she answered honestly. It had never even crossed her mind.

"They've been in the music industry much longer than we have," Jeanette added logically. "So of course they have more fans and money."

"But if we work extra hard," Brittany suggested quietly, "we could probably become just as famous as Alvin."

"Is that what this is about?" asked Jeanette. "Alvin?"

"_No_," Brittany hissed.

"You two are way too competitive," Eleanor groaned. "It's the weirdest way of flirting and Jeanette and I have to suffer for it."

"It's _not_ flirting!" Brittany snapped.

"But you like him, don't you?" Jeanette said quietly.

"No," Brittany replied, her cheeks turning the faintest shade of pink.

"It's okay," Eleanor said cheerfully. "I have absolutely no problem with admitting that I like Theodore. He's just so adorable!"

"In my opinion," Jeanette offered hesitantly, "Simon Seville is quite dreamy."

"I _don't_ like Alvin," Brittany repeated dully. "And you two shouldn't have crushes on Simon and Theodore either."

"You can't tell us who to like, Britt," Eleanor said primly.

"You want to be the best singers out there, don't you?" Brittany demanded.

"Of course," Eleanor replied.

"Well then, Alvin and the Chipmunks are the only ones standing in our way of that!" Brittany stated, folding her arms over her chest. "

"That doesn't mean we can't be friends," protested Eleanor. "Didn't they take us in? They're letting us live in their own house!"

"They did that so _this_ could happen," Brittany scoffed, gesturing toward her sisters. "The Chipmunks can afford to be friends with us because right now, they're on top. We have to change that, girls."

"You sound like Ian Hawke," Jeanette said flatly.

"I'm not Ian," Brittany retorted, "I'm your sister. I've always wanted what's best for us, and I always will. You're not going to let one stupid crush ruin our sisterhood, are you, Jeanette?"

Jeanette gasped. "Of course not!"

"And neither would you, right, Ellie?" Brittany turned to the green Chipette.

"Eleanor's eyes widened. "No way!"

"Let's make it official," Brittany said, the steel in her baby blue eyes visible. "We, the Chipettes, promise to not let boys and things like crushes or love get in our way of becoming the ultimate superstars."

"Promise," Eleanor squeaked enthusiastically.

"I promise," Jeanette said softly.

"I promise, too," Brittany declared. "And let's not tell anyone else about this, okay?" she added hastily.

"Okay," Eleanor agreed again, as always.

Jeanette stared at Brittany for what seemed like an eternity before she said, "Okay."

While Brittany and Eleanor eagerly left the studio to get on with whatever they had planned for the rest of the day, Jeanette stayed. Sh sat on the floor, silent and still, and thought long and hard about the promise she had just made.

* * *

**Loved it? Hated it? Constructive criticism? Anything is appreciated! And I'll try to update as soon as possible, since I've already had the whole story written out by hand, I just have to type it up and then upload into my doc manager. Thanks so much for reading! **


	2. Brittany's Emotional

**Okay, chapter 2! This mostly focuses on Brittany and Alvin, with a little Jeanette and Simon. Sorry for the Theodore/Eleanor fans, that doesn't happen until much later, AFTER Eleanor goes through a crisis. I can't say anymore or I'll spoil the story. R&R, please! 3**

* * *

**CHAPTER 2**

"Pass me the butter, would you, Theo?" Eleanor asked, looking at her slice of dry toast.

"Sure, Eleanor," Theodore replied, handing it to her.

"Do you _really _have to eat that, Ellie?" Brittany asked. She motioned to her and Jeanette's empty plates. "We could be rehearsing."

"That's all you Chipettes ever do anymore!" Alvin complained. "Rehearse."

"So?" Brittany challenged. "What's it to you if we're serious about our singing career?"

"We are too," Alvin argued. "But we still do other stuff than spending all our time in the studio."

"Well, we're not _you_," Brittany sneered dismissively. By this time, Eleanor had finished up her buttered toast. "C'mon, girls, let's go."

"You sure you don't wanna do something fun today?" Alvin called as they left the kitchen in a neat little line, Brittany in front. "We could go to a water park."

Eleanor halted. Her ears perked up. "Water park?"

Brittany bristled. "They just want to see us in our swimsuits, Ellie. We have better things to do."

"You mean like sing the same song over and over and over again?" asked Theodore. He hadn't meant to sound sarcastic, but that's really what rehearsals were.

"It _is _supposed to be a 97 degree day, Britt," Jeanette pointed out. "A good day to go to a water park, if you ask me."

"Then everyone will be there," Brittany shot back, refusing to give in. "It'll be crowded and the lines will be long and no fun at all."

"We're small though," Simon said. "And world famous. That ought to help in both cases, don't you think, Brittany?"

"I DO think!" Brittany shouted at Simon, tears visible in her eyes. "Fine, all of you go to that stupid water park and – and I hope you all DROWN!"

She ran out of the kitchen before anyone could say another word.

"I … didn't mean it that way," Simon said quickly. "All I was saying was that -"

"Don't worry, Simon," Jeanette said comfortingly. "Britt probably wasn't having a very good day. She can get really emotional at times."

"Way to go, Simon," Alvin said sarcastically. "You made her _cry_. I'll go see if she's okay … you know … just in case." He scampered off after Brittany before anyone could ask him why he'd suddenly taken an interest in the pink Chipette's wellbeing.

Predictably, Alvin found her in the studio. It was obvious that she had been crying, but it was also obvious that she had tried – and failed – to cover it up.

"Britt?" he called out to her.

"Go away, Alvin," she snapped at him.

He ignored that. "Are you okay?"

She turned her face away from him and folded her arms over her chest in annoyance. "Yes, Alvin, I'm fine. Now _go away_."

Alvin shrugged nonchalantly. "I guess Jeanette was right. You really are emotional."

As he'd expected, Brittany looked pretty riled up. "Why would Jeanette say that? I am NOT emotional! Did you hear me, Alvin? I – AM – NOT – EMOTIONAL!"

"Okay, okay," Alvin held his hands up in surrender. "I get it."

Brittany's shoulders sagged and her tail slumped down. It looked as though she was about to cry again. Hesitantly, Alvin walked up and sat down next to her.

"You wanna talk?" he asked softly.

"No," sniffled Brittany, determinedly looking away from him.

Carefully, Alvin put his arm around her, forcing her to turn her head at him when she glared. He just grinned and kept his arm where it was.

"C'mon, Brittany, what's wrong?" he repeated. "You don't just break down and cry for no reason."

"I'm just … really stressed," Brittany said in a monotone.

"About what?" Alvin asked incredulously. "There's nothing important coming up. We've already won the International Music Awards."

"That's not it," Brittany sighed. "And I can't really tell you ..."

"Why not?" Alvin asked curiously.

"Because I don't break promises, that's why," Brittany snapped, rebooting back to her lead-Chipette-attitude.

"What promise?" Alvin tried.

"Can't say," replied Brittany testily. She wriggled out of Alvin's arms and stood up. "We should go back."

"Go back where?"

"Back to the others. You're really slow, you know that, Alvin?"

"I've been told," he answered with a smile, showing that he wasn't letting Brittany's insults get to him.

"By Simon?" Brittany asked, apparently interested in the conversation now.

"Who else?" Alvin replied calmly. "Besides you, of course," he added teasingly.

Brittany blushed. "I didn't mean that."

"It's okay," Alvin said, waving off the half-apology. It was pretty much the best you got from Brittany Miller.

"Let's go back," the Chipette repeated.

"Sure," Alvin replied, getting to his feet. He was still completely confused as to what had just happened – the whole 'secret promise' thing and Britt's mood swings hadn't really helped – but he'd go along with it.

In front of Brittany, anyway.

"But first," Brittany paused, "I need to fix myself up in the bathroom."

"Ummmmm," was Alvin's genius response.

Brittany tilted her head to the left and widened her baby blue eyes at him. She looked absolutely adorable.

"Wait for me?" she asked.

He nodded and she flashed him a megawatt smile – one of the reasons fashion magazines loved to put Brittany on their cover. The smile lured people in.

Alvin sat back down as Brittany flounced out of the studio to the bathroom, where she could 'fix up' her already flawless face, so no one would know that confident Brittany Miller had been crying.

_There's a lot going on underneath that perfectly put together surface, isn't there? _Alvin thought. _I really should get to know Britt better … and the bet! I forgot to ask her out!  
_

* * *

In the kitchen, Theodore and Eleanor were playing tic-tac-toe on a napkin. Instead of X's and O's, Theodore played with smiley faces and Eleanor with hearts. It was their fourth game (Eleanor had won every single one so far) and Theodore was losing.

Jeanette and Simon sat side-by-side on the edge of the kitchen countertop, watching them. Neither of them had said a word to each other since Alvin had gone chasing after Brittany.

Jeanette was swinging her legs and softy humming "Put Your Records On." Nervously, Simon fidgeted, pushing up his glasses every so often. He had no idea what to say to Jeanette to strike up a friendly conversation.

_Or you could just ask her out_, he reminded himself. _That's the first step to making her your girlfriend. _

But he wasn't brave enough to do that yet. He didn't even know if the blue Chipette considered him even one of her friends.

"Simon?" she said, forcing him to jerk his head up and look at her. "Are you alright? You look a bit … nervous."

"Yeah, J-Jeanette. I'm fine," Simon stuttered. On the bright side, though, at least she'd started the conversation for him!

"If you're worried about Brittany, I'm sure she's okay," Jeanette said sweetly. "You didn't say anything mean and I bet she's not at all mad at you."

Simon decided it was smartest to pretend that this was what was bothering him. He breathed out in fake relief. "That's good. The last thing I wanted was an angry Brittany."

Jeanette gave him a small smile and they lapsed into awkward silence again.

"What?" Theodore cried. "Eleanor! How are you so good at this?"

Jeanette leaned over so she was right next to Simon and whispered, "Safe bet to assume that he lost again, huh?"

Simon smiled and then blurted out, "Hey, Jeanette. Maybe we should go check up on Brittany? Since she hasn't come back yet ..."

"Alvin's already gone to do that, Simon," Jeanette replied in a tone that he couldn't really tell if it was friendly or not. "So I'm sure he's with Britt and she's fine. No one wants to be crowded by people when they're not in a good mood."

"Right," Simon agreed. It had actually been a ploy for him and Jeanette to go somewhere private. But of course she wouldn't have known that.

Thinking over how he could rephrase what he'd just said, it suddenly hit him – he was making it seem like he was infatuated with Brittany! No wonder Jeanette had been speaking to him in a strange voice that last sentence.

Now, how to put it right? Simon opened his mouth to say something crazy – ask her out – but then Alvin and Brittany walked in, side-by-side.

He absolutely could not ask her out in front of Alvin. If she said no, Alvin would never let him hear the end of it.

"Brittany!" Jeanette cried out immediately, full of concern. "Are you okay?"

"Fine, Jeanie," Brittany replied loftily. "Thanks."

"Do you still not want to go to the water park, Britt?" Eleanor pouted. "Because I guess we could rehearse ..."

Brittany plastered on a big, obviously fake smile. "No, I think we could all use a day off. You guys head down to the water park yourself. I think I'll stay here and take a nap."

Jeanette and Eleanor exchanged meaningful glances. "I don't think I want to go anymore," Eleanor announced.

Theodore looked crestfallen. "Me neither."

"I suppose I'll have to stay home to take care of all of you," Alvin said, making up an excuse to spend extra time with Brittany.

"I'm sorry, Simon," Jeanette looked at him as though this was the last thing she wanted to say. "I think I'd better stay here with the rest of the Chipettes."

"I'm sorry, too, Simon," Brittany piped up. "I totally overreacted about what you said. I take it all back."

Simon barely heard Brittany's apology. He was too busy silently screaming at Jeanette from his head. _You don't always have to do what everyone else wants! You're not attached to your sisters at the hip, Jeanette!_

But on the outside, all he said was, "I definitely don't want to go by myself. And Dave's not even up yet, so how would I even get there? I'll just hang out here with all of you."

"Well, I'm going up to my room," Brittany announced after a moment of all of them standing in the kitchen in awkward silence. "To take my, um, nap."

"I'll go with you, Britt!" Eleanor added, bouncing after her older sister.

"I should probably, um, go with them," Jeanette stuttered, giving what seemed to be only Simon a quick little wave. Then she turned around, almost tripping over her own feet, and followed her sisters out.

"Aren't they a clingy bunch," Alvin muttered under his breath, summing up Simon's thoughts exactly. "It's like a game of follow the leader."

_And Brittany always leads, _Simon added bitterly in his head.

* * *

**Loved it? Hated it? Constructive criticism? Anything is appreciated! **


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